How Do I Manage First Date Anxieties?

Estimated reading time: 15 minutes

Hi Doc,

This is my first time seeking dating advice, so I apologise if I’ve made a mistake here. I’m just looking for some advice. If I’ve written too much here or jumped the shark please do stop here and I’ll understand. 

I recently went on a date with a guy I matched with on Tinder who I’d been chatting with for a couple of weeks beforehand. The chatting went very well, nothing out of the ordinary except I could tell we had a lot in common and it felt very easy to talk to him. In fact, I had no reason to worry at all and so I was excited for our first date but not to the extent I had put any pressure or stress on myself. For me, this was a first date amongst many and though I had hopes I was feeling relaxed.

The date went incredibly well, the guy was funny and charming. He asked me lots of questions and seemed genuinely interested in my responses. We got on brilliantly and more than anything he made me feel calm and safe. The date taught me how good a good date can feel, especially after many bad dates. For somebody who tends to pick up on bad vibes most of the time, it has felt amazing to affirm to myself that this guy maybe likes me. 

After the date he messaged me asking to see me again which has been the first time that has happened in a long while. I have of course agreed and we’ve continued to chat. However, the problem has arisen where I’m starting to feel very anxious now, I’m worried that I can’t replicate the success of the first date. Furthermore, as we won’t be be seeing each other for another week I’m already starting to feel our chat is not as good as it was, that I’m running out of things to say and I fear we’re boring one another. Conversely, I’m also anxious that I might already be attempting to ‘binge’ on him.

Do you have any advice on how I can suppress these anxieties and should I back off? The last thing I want to do is scare this guy off, how do I navigate this post-first date minefield? 

Even My Butterflies Have Butterflies

Ah yes, Chronic Overthinking Disorder, I know this well. So well I could probably coach it at the Olympic level.

So, in case it’s not obvious, EMBHB, you’re seriously overthinking this. And it’s not like I can’t empathize; overthinking, especially when it came to relationships, was one of the worst parts of the rejection-sensitive dysphoria that came as part of the ADHD bundle. Which is actually as good a place to start as any.

Overthinking and overanalyzing, especially when you’ve had a good experience after many bad ones, is a sort of self-protection. There’s often a part of you that’s so used to disappointment or being let down or hurt, that you’ve ended up with a sort of hypervigilance; you’re constantly on guard for that next potential threat or next potential heartbreak. So when something good happens and you’re pleasantly surprised, there’s a part of you that’s still pretty sure that this good thing couldn’t possible be legit, or if it is, there’s a hidden catch that you haven’t seen. So you stay worried that something is going to screw it up. Either there’s a shoe waiting to drop, or you‘re going to do something and wreck everything and thus snatch defeat from the jaws of victory.

Now to be fair, being on the lookout for something awful has – and likely has had – actual benefits. If you’ve been hurt before, especially repeatedly, then keeping a watchful eye out for other red flags and warning signs helps keep you safe and lets you avoid unnecessary heart break. It is likely that this is a pattern that’s served you well before. But the problem is that vigilence and threat detection sometimes goes into overdrive. In the way that sometimes our immune systems can go overboard and respond to things that aren’t actually harmful, that hypervigilance can end up pinging on things that aren’t actually problems. And in a matter of irony so cruel it almost seems deliberate, by trying to keep ahead of anything that could possibly go wrong, you end up causing the very event you were hoping to avoid.

It’s like the world’s most pathetic Greek tragedy in some ways.

I mention this because it’s important to recognize that just because your brain is convinced that you’re standing on the precipice of screwing up a good thing, that doesn’t mean your brain is right. It’s just trying to protect you, in it’s weird, over-zealous way, like a dog barking at Amazon deliveries. It’s one thing to trust your gut, but that really only works when your gut is actually trustworthy.

So I want you to keep that in mind when you think about what to do next. And the next thing you need to do is… well, honestly, very little. I won’t say you need to do nothing, but you certainly don’t need to tie yourself into knots trying to make things perfect, or near-as dammit.

Here’s the thing: you don’t need to replicate the success of your first date. That’s not what he’s hoping for, nor is that what you should be trying to do. This is very much a case of “Do, or do not. There is no ‘try’”.

Part of this is because you first date was, in its way, not the first date but an audition. You and your guy were seeing if there was mutual compatibility and in-person chemistry, especially after a couple weeks of messaging back and forth. There was clearly plenty of both, seeing as you both had a good time and he asked you out on another date.

That you shouldn’t try is because of what actually made that first date successful: you were relaxed. You were, simply, not trying. You were just being. You weren’t worried about making sparkling conversation or impressing him or convincing him that you were special. You were – as the cliche goes – just being your best self and living in the moment. No analyzing every word before it left your mouth, no trying to gauge his every microexpression to see if he was into you or not; the two of you were just vibing, and the vibes were good.

And that’s what made it work. And hey, that’s all you need to do for next time.

Everything else – worried that a week is going to be too long, worrying about the quality of your conversations, and so on – is just that part of your brain trying to protect you from heartbreak and disappointment. All you need to do now is turn the volume down a few notches. Not even off – God knows that’s hard enough – just down.

How do you do that? You put yourself in the mindset that he already likes you and act like he’s a friend you already know. Not in the “put him in the Friend Zone” kind of way, but by assuming the level of connection and surety you have with your friends already. If you can have times when you and your friends don’t message or talk for a day or two and can let the conversation just ease to a halt for a bit before picking it up later, then you already know how to do this.

You presumably don’t feel like you need to be dancing as fast as you can to keep your friends in your life, lest they grow bored and leave. The same applies to this guy. If he was into you enough to plan another date soon after the first one? Then you don’t need to be keeping him entertained by staying at a level that you can’t possibly maintain for long without serious strain. You can continue to be the relaxed, fun person who he went on that first date with. You know: the person who he clearly connected with and is into.

If you don’t have anything to say at the moment, then hey, that’s ok. You aren’t his cruise director; you don’t need to be keeping him constantly entertained. You don’t want to give off a “disinterested” vibe, but it’s ok to let the conversation come to its natural conclusion. In person, this can be companionable silence; via text, you can convey this by saying “hey, I need to get back to $TASK, talk to you later?” This gives you and him both the opportunity to re-engage later on, when it’s convenient for you both. You can even demonstrate that you’re still interested by referencing something else you two had talked about earlier –  “Hey, you said X and Y about Z… Check this out, I just read this thing about Z…”

(It’s easier to let things trail off when you know each other and feel more secure in things; for now, you’re functionally saying “I would like to keep things going, but I have responsibilities I can’t ignore and I don’t want the time pressure building while we talk and making it less fun for us”)

And honestly, a week between dates is nothing, especially as you get older and responsibilities pile up. I understand the fear of losing the emotional momentum. But at the same time, you have to trust that you and he had a good enough time that he’s not going to forget that he had a good time with you if you’re not continually reminding him of your existence. While I understand the anxiety of whether someone might find another match in the interim, the underlying logic ultimately gets distilled down to  “OK, he’ll choose me as long as I ensure he’s too busy to check out other options“. Even when that’s coming from as pure and well-intentioned a place as possible, that’s an exhausting way to live.

You have to have enough faith in your own awesomeness – and his ability to perceive your awesomeness – that you can remind yourself he’d be crazy to pass you up. And if he does… well, that’s his loss, isn’t it? 

As hard as it can be at times to believe, you can’t really critical-path your way to a relationship. There’s no way to make dating an error-proof experience, or to guarantee that things won’t go wrong. As the man says: it is possible to commit no mistakes and still lose. That’s life. You can’t control for everything and you’ll drive yourself mad if you try. At a certain point you have to just let go and let God. Or The Doctor, or the universe or the Force or whatever.

So for now? Look at your hypervigilance on this as a sort of self-protection, thank it for the way its protected you before, and then just let yourself relax and just be. It was that same relaxed self your date was into; remember that, tap into that and let things flow from there.

Good luck.

Hi Doctor NerdLove

Over the past year, I have been making an effort to get out more and be more social / make new friends with people and have found my place in a group that I hang out with often now. I kind of came in at just the right time for one of the women in the group, and managed to be of good help to her. Just before we met she underwent a toxic breakup with a boyfriend, I and the rest of the group had to help her come to realize was abusive and had her previous social circle collapse soon after. She was in a pretty bad place and needed some friends who could lift her up and be a set of open ears. Come Christmas, she even left me a handwritten note thanking me personally for everything I’ve done for her this year. I’m glad I was able to help her through all this.

Now after a few months of getting over everything, she’s moved on from her ex and just started dating a new guy. This should be great and I want to feel happy for her, but I can’t help but feel jealous at her almost instant-seeming success. I’m someone who’s always been cool with making friends with women but have never been able to land a date, much less a relationship. She’s a very attractive girl while I’m a pretty below-average guy that’s been slowly trying to get in shape and better groom myself. I had gotten pretty vulnerable with her while hanging out and opened up to her about my own struggles with loneliness, isolation, and depression, and while she didn’t really have anything new to say she was very kind and reciprocating in lending an ear to me. Now that she’s had her success and my own jealousy has set in, I worry about falling into the “crabs in a bucket” mentality since talking about her problems with her brought me a strange sense of peace. It was nice in a way to have someone I could help and listen to who was having problems in a similar ballpark as me, but now she’s fixed many of those and I’m still here trying to pass the starting line.

I know some might see this as me having feelings for her, but it’s genuinely not the case. I was attracted to her when I first met her but realized soon that things wouldn’t work out for us in that context. She wants to feel “protected” by her partners, wants a more stoic guy, and likes being the receiver/responder in a relationship as opposed to the initiator. I’m not that guy and I (imagine I’d) like more assertive partners as well, so I let all of that go a good while ago. Still continued to meet new people and ask others out, but still no luck.

I just want to figure out the best way to deal with these emotions and don’t want to hurt her after she’s come so far.

Thanks!

Is This Envy?

Here’s a question, ITE: what are you afraid that you’re losing, here?

I’m not asking to put you on the spot or question your position that this isn’t about your having non-platonic feelings for your friend, I’m asking because it’s good to zero in on precisely what you’re worried about that’s causing these feelings.

As a general rule, jealousy and envy are like check-engine lights – a sign that there’s an underlying need that isn’t isn’t being met. Sometimes that need is one in the relationship; you’re feeling distanced from your partner, you aren’t getting the level of connection or affection you are used to, and so on. Other times, it’s a need within yourself, and often one that you were looking to an outside source to fulfill. When we feel that the fulfillment of that need is in danger, that fear of impending loss tends to manifest as jealousy.

But jealousy or envy don’t actually tell you what the problem is. Just as the check engine light could be anything from “your engine’s about to fall out of the car” to “you didn’t tighten the gas cap”, feeling jealous or envious can come from a multitude of places, many that aren’t immediately obvious. You want to get in under the hood and figure out what made the light come on.

From your letter, it sounds like at least part of it is that sense of not being alone in your struggle. Having a comrade in arms, as it were, made you feel more connected and less isolated, like there were other people in the world who could understand you. Her success, then, would seem to diminish you, leaving you alone once more.

But maybe the issue here is that having a comrade in the “not doing so great at dating” trenches isn’t what you need, certainly not long-term. I can’t help but suspect that the issue was the closeness with your friend. You bonded over your respective dating woes, sure, but that was the catalyst for the connection. Maybe what you’re missing isn’t someone who’s in the same hole as you but just that close, open and emotionally intimate connection with another person. Now that she’s dating someone else, you’re worried that this connection is in danger and you aren’t going to have someone that you can be vulnerable with.

I suspect that this ties into your effort to be more social and make more friends, more than your success in dating or lack thereof. A lot of straight guys, quite frankly, don’t have close friends. In fact, we’re especially prone to loneliness and emotional isolation. Straight men are actively discouraged, both subtly and overtly, from having close, emotional friendships with others, especially other men. We’re only “allowed” to have it with people we might potentially fuck, and even then it gets a bit of side-eye from folks. Chalk it all up to toxic masculinity shitting in the punchbowl again.

While I’m certainly cheering for you to improve your dating life, I don’t think that’s necessarily the answer to the problem here. I don’t think that having more dating success would resolve the feelings you’re feeling; I strongly suspect that you’d find yourself in a similar boat, just with someone you were dating, instead of a friend. I think what you need more than anything else, are more friends, and closer ones.

Fortunately, you’ve already got a head start there; you found a pretty cool group that you hang with. You have opportunities to become closer with other people in the group. Sure, circumstances lead to your closer bond with one person, but honestly, this proves you can do it in the first place. I think, if given the time and opportunity, you could become closer with others in the group as well. That, I think, would be a good use of your time.

Now, what I don’t recommend is focusing on bonding with other folks over relationship struggles. While yes, that shared point of reference can be an easy way to bond with them, bonding over negatives has an amplifying effect. It’s been my experience that when the point of your connection is “well, we’re all stuck in this hole, but at least we’re stuck in it together”,  this creates a sort of learned helplessness. The friendship becomes less about being stuck in the hole, rather than getting out of it at all. Then, when someone actually starts trying to get out – or worse, succeeds – it threatens the rest of the group’s self-identity as being stuck. Then you get the crabs-in-a-bucket effect, as everyone tries to drag that person down and reinforce the idea that you’re stuck and there’s no way out.

And if you let that go on long enough, the whole thing curdles and becomes toxic. And it’s not like we haven’t seen where that ultimately leads.

The other thing I would suggest is that you actively continue to be friends with your no-longer-in-the-struggle buddy. The fact that she’s dating again doesn’t nullify your friendship; your mutual travails were simply what brought you together in the first place. If you have enough mutual interests and (platonic) chemistry, then the initial catalyst doesn’t need to be the only thing that you base your friendship on. If you can see that her dating success doesn’t take away from your efforts, nor does it actually threaten your relationship, I think you’ll find that sense of jealousy will start fading away.

But again: that’s in addition to working on making closer friends and continuing to improve your dating life. The whole “don’t put all your eggs in one basket” thing may be a cliche, but its a cliche for a reason. Having a wider foundation of support is invaluable and leads to stronger, sturdier relationships over all.

So work on building that foundation, ITE; I think you’ll find that it makes everything in your life better, not just these complex feelings you’re having.

Good luck.